Character education has the potential to increase student academic performance as well as social and emotional skills regardless of socio-economic level, race, gender, or grade level. Yet prior theory and research suggests there is a lack of preparation for educational leaders in developing and implementing aspects of character education. Most educational leaders are tasked with creating their own programs to encourage character education within their learning organization. The purpose of this dissertation study was to examine key strategies and challenges when developing and implementing aspects of character education in a high school setting from the perspective of the school principal. Data were collected and analyzed as part of a qualitative narrative inquiry study. Three high school principals from a major metro southeastern city were interviewed twice. These interviews were conducted to gain insight into the stories and experiences of developing and implementing aspects of character education. The study found that involving all members of the learning community and positive praise were the main indicators of success with implementing character education. The largest challenge identified was the lack of preparation for educational leaders towards the development and implementation of character education. Furthermore, recommendations are provided for future practice and research. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]